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Aminomethylation of Thioureas with N,N-Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange

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Abstract

The O-triethylsilylated hemiaminal Et3SiOCH2NMe2 readily transfers the Me2NCH2-group to various thioureas under mild conditions and without catalysts or co-reagents. In the reaction with PhNHC(=S)·NHPh, the initially formed mono-substituted derivative PhNHC(=S)NPhCH2NMe2 readily rearranges to produce the unsymmetrical thiourea PhNHC(=S)NMe2 and hexahydro-1,3,5-triphenyl-1,3,5-triazine.

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Acknowledgments

This research was supported by the Welch Foundation (Grant AH-0546). J. M. acknowledges the Student Finance England loan to cover the academic year 2017–2018 study abroad from Newcastle University. We also acknowledge the NSF MRI Program (CHE-1827875) for purchase of the Bruker Venture and the Kresge Foundation for an NMR maintenance endowment grant.

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Authors and Affiliations

  1. Department of Chemistry, The University of Texas at El Paso, El Paso, Texas, 79968, USA

    J. McMahon, H. K. Sharma, A. Metta-Magaña & K. H. Pannell

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  1. J. McMahon
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  2. H. K. Sharma
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  3. A. Metta-Magaña
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  4. K. H. Pannell
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Correspondence to K. H. Pannell.

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No conflict of interest was declared by the authors.

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This article is dedicated to many excellent Russian exponents and proponents of organosilicon chemistry, past, present, and future.

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McMahon, J., Sharma, H.K., Metta-Magaña, A. et al. Aminomethylation of Thioureas with N,N-Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange. Russ J Org Chem 55, 1764–1771 (2019). https://doi.org/10.1134/S1070428019110198

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  • DOI: https://doi.org/10.1134/S1070428019110198

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